Many systems utilize wiring to route power, electrical signals, etc. To simplify manufacturing and maintenance of such systems, several wires may be coupled together to form a wire bundle. For example, a set of wires that extends from one device to another device may be assembled into a wire bundle so that each of the individual wires do not have to be routed independently. If a particular set of wires is intended to connect to a single device, it may be convenient to terminate the wire bundle with a connector such that each wire corresponds to a contact of the connector. The connector may allow all of wires of the particular set of wires to be connected to (or disconnected from) the single device at the same time. Such wire bundle and connector arrangements are common, for example, in aircraft, automobiles, building systems (e.g., air conditioning and heating systems, etc.), and many other fields. Despite the prevalence of wire bundle and connector arrangements, testing schemes for assembled wire bundles and connectors are generally manual.